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Casiola Vacation Homes is Taking Short-Term Rental Management to the Next Level

Casiola Franchise

Dennis Goedheid and Russ Kraft discuss transforming a small property management business into a growing franchise system.

When Dennis Goedheid purchased a 25-home vacation rental business in Florida after exiting his on-demand printing company in Belgium in 2013, he had no idea how much work – or opportunity – lay ahead of him.

“Property management and vacation rentals seemed like something fun and easy to do. I envisioned myself sitting at the pool all day here in Florida with a cocktail and my laptop, waiting until someone would need something,” Goedheid says, recalling how little he knew about the demands of property management at the time.

But then reality set in.

After spending his first six months as a property manager working “nonstop, 24/7” alongside his wife, who helped Goedheid run the new business, the couple thought they’d finally managed to secure a day off to enjoy a day trip together in Clearwater. Only 15 minutes after arriving at the beach, though, a guest called with an urgent problem: They’d locked themselves out of their rental home and needed assistance getting back inside.

Forced to cut their day trip short and make the 2.5-hour drive back to Orlando, the Goedheids knew something needed to change about their new business situation – and quickly.

“That was the point that I told my wife, look, this is just too hard. We either sell the business and look for something else, or we grow and scale so that we can hire employees and we don't have to do everything ourselves anymore, 24/7 because this is not a life,” Goedheid recalls.

Firm in his belief that the vacation rental management space offered a wealth of opportunity under the right circumstances, Goedheid chose to focus on growth – and bringing the vacation rental investment and management industry into the 21st century.

A Growth-Oriented Mindset

Despite Goedheid’s lack of familiarity with the U.S. property management industry, his experiences in Belgium’s printing industry, composed mostly of fragmented small businesses, helped him recognize the shift that was taking place in Orlando’s vacation rental space in 2014 – and sparked an idea that would ultimately change the direction of Goedheid’s career as the founder and CEO of Casiola.

“I could see a consolidation happening there – movement toward professional managers, more online. … With all the know-how and experience I had before, running an ecommerce business, I thought, ‘If we can apply this to this new industry, we can really make a difference,” Goedheid recalls.

It didn’t take long for Goedheid’s plan of offering technologically connected vacation rental management services to property owners in Orlando to succeed. Over the next few years, Casiola expanded from 25 rentals managed by Goedheid and his wife to a company with 85 employees and nearly 350 properties – and counting.

Rebounding - and diversifying

Despite the growth the brand experienced for over half a decade, things changed in 2020 when pandemic lockdowns brought the tourism industry to a near-standstill. Even after cities across the nation reopened later that year, vacationers continued to exercise caution in their destination choices – often overlooking Orlando for more secluded locales.

“People wanted to go to more remote areas, like mountain destinations or beach destinations. Big tourist destinations like Orlando or urban markets were really hit hard and took a little bit longer to recover. We saw, as a business, that it was important to diversify and be active in different markets and not just put all our eggs in one basket and only manage vacation rentals in Orlando,” Goedheid says.

Recalling that property managers and entrepreneurs had called over the years asking about licensing under the Casiola brand in locations beyond Orlando, Goedheid decided to meet with a prospective business partner in Aruba.

“I saw that there was so much potential on the island. There were a couple of property managers, but they weren't operating as professionally as most of the managers here in the U.S. There were a lot of synergies that we could bring software processes to that they were not doing yet. And so, at the end, we decided hey, let's start a joint venture,” Goedheid says.

Within two years of that partnership, which combined Goedheid’s expertise and Casiola's software with the small vacation rental business’s local network and contacts in Aruba, the venture grew from 15 vacation homes to nearly 100.

“Although it (was) not a franchise, that first destination made it clear for us, if we can do it there, we can probably replicate that and help other businesses in other destinations to do the same. So that's how we came to the conclusion that a franchise may be a good option for us,” Goedheid recalls.

Taking Property Management and Technology to the Next Level

Earlier this year, Casiola offered its first franchise opportunities with territories in the U.S., Caribbean, Central America and Europe – along with a focus on giving new franchisees a competitive edge with the brand’s unique software.

“One of the things that Casiola does really well is the operational software in the homes. Everything from housekeeping to maintenance – it's just super tight,” says Russ Kraft, Director of Franchise Operations at Casiola, who has worked as a general manager in operations for 25 years.

That innovative custom technology is based, at least in part, on Goedheid’s experiences learning about the tedious realities of property management back in 2013 – and a desire to streamline the experience for franchisees and employees at Casiola today.

The brand’s innovative suite of systems includes platforms for property owners to receive photo inspection reports, guest check-in notifications, feedback, reviews, communications between owners and managers, and more in real-time – offering a competitive advantage for franchisees.

“By using our processes, software and our knowledge, I think you can get a head start of three to five years,” Goedheid says.

Finding the Right Fit

When it comes to franchising, the team at Casiola understands that finding the right candidates is important – for their own success as well as that of their franchisees.

“When you have an operation that has just a few people, and everybody's trying to wear (every) hat, it doesn't often work really well. And so, a lot of times, you kind of just sit there at that level of 10 or 15 homes and you just can't get over the hump. Our perfect candidate would be that type of company that they really want to be in this business, but they're frustrated. They can't get to that next level,” Kraft says.

Other qualities the brand looks for in candidates include well-maintained properties and the ability to maintain high standards consistently in every market.

“(Vacation rental management) was a big learning curve. … It took a long time to figure it all out and set it up. If we can do that from Day One (for franchisees), that's going to make such a big difference. And we see that in the areas that we already access – we were able to double the business in a matter of months,” Goedheid says.

While business advantages are key when it comes to building a franchise, Goedheid says the work he and the Casiola team do together goes beyond business – it’s also personal.

“We're still doing it because it's such a fun business. People are happy, they're on vacation. You help them build memories. A vacation to Disney World with the whole family that people book a year in advance – we can help them in the planning phase, creating an experience that they’re never going to forget in their lives,” Goedheid says.

To learn about franchising opportunities at Casiola, visit

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